Sodium Iodide → (R)-4-((R)-1-(7-iodoquinolin-5-yloxy)ethyl)pyrrolidin-2-one

HRID 1402717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402717
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)[CH3:14])[CH:3]=1.CNCCNC.[I-:27].[Na+]>O1CCOCC1.C(Cl)Cl.[Cu]I>[I:27][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)[CH3:14])[CH:3]=1

Komponenten

7

Edukt 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 71238288(R)-4-((R)-1-(7-bromoquinolin-5-yloxy)ethyl)pyrrolidin-2-one

Produkt 1

HCID 71238317(R)-4-((R)-1-(7-iodoquinolin-5-yloxy)ethyl)pyrrolidin-2-oneAusbeute 26,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

50 mg of Example 27 and 9 mg of copper (I) iodide were suspended in 300 μL dioxane under argon. 9.6 μL N,N′dimethylethylendiamine and 45 mg of sodium iodide were added and the mixture heated to 110° C. over weekend. The mixture was diluted with DCM and extracted with aqueous ammonia and water, the organic phase was subsequently concentrated in vacuo and the residual purified with HPLC (XbridgeC18; MeOH/water, TFA) to yield 15 mg yellow solid as Example 37.

Aufarbeitung

  1. extractionextracted with aqueous ammonia and water
  2. concentrationthe organic phase was subsequently concentrated in vacuo
  3. customthe residual purified with HPLC (XbridgeC18; MeOH/water, TFA)

Quellen und Nachweise

ORD-Eintrag
ord-38143c106d78469bbbdfdcfe43a0c4b3
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912173B2

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